Litigating cross-border civil disputes involving foreign parties, foreign conduct, or foreign courts requires a unique set of skills and knowledge. Such transnational cases are procedurally and substantively complex and may create intricate ethical issues for U.S. lawyers. This Article examines a set of both common and innovative strategies that were used in the disputes arising from Texaco’s oil extraction operations in the Ecuadorian Amazon basin of Lago Agrio. The cases brought against Texaco and its successor Chevron Corporation span over two decades and cumulatively involve most, if not all, litigation strategies available for cross-border disputants. By analyzing these strategies in their broader procedural context and focusing, in part, on the decision makers behind them, this Article highlights potential challenges and pitfalls in international dispute resolution. The Lago Agrio litigation serves as a cautionary tale that aggressive litigation strategies, dilatory tactics, and gamesmanship, regardless of their short-term success, can result in exorbitant costs, overlook the wider economic impact of protracted litigation, and undermine the parties’ long-term business interests.